


Flowers on the Window Sill

by versaillesatnight



Category: Gilmore Girls, Supernatural
Genre: Fluff, M/M, POV Outsider, Pre-Series, disgusting fluff
Language: English
Status: Completed
Published: 2015-04-01
Updated: 2015-04-01
Packaged: 2018-03-20 16:45:59
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,962
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3657813
Author URL: https://archiveofourown.org/users/versaillesatnight/pseuds/versaillesatnight
Summary: <blockquote class="userstuff">
              <p>Sam and Dean Winchester's relationship as observed by the good people of Star's Hollow.</p>
            </blockquote>





	Flowers on the Window Sill

**Author's Note:**

> Okay so......this is a Gilmore Girl's wincest crossover. Which I figure there has to be someone other than be into that. It only very vaguely mentions Dean Forester, and I'm pretending that his similarities with Sam Winchester are just not noticed by anyone. This is almost 4,000 words of Sam and Dean interacting and being cute about each other. The title is from, what else, Where You Lead by Carole King. Also this is like TRAGICALLY unbetaed like I just wanted to write a Gilmore Girl's crossover cause Gilmore Girl's has literally consumed my life so this was more fun than anything. ANYWAYS I hope it's still an enjoyable read!!

Kirk is the first one to meet the new family. He unlocks their apartment for them, props the door open as they work their way inside, tugging too-large bags through the pretty blue doorframe.

            “I think you’ll find it cozy and incredibly quiet,” Kirk says, “I thought about living here for a few days, but my mother told me it’s not the best part of town.”

            The father of the group, said his name was John, seems not to hear him, but one of the boys chuckles low, elbows his brother, “Guess we’re roughing it for a few days, Sammy.”

            “If you have any trouble at all, please, do not hesitate to call. Or email. Or fax. Letters usually are delivered next day, so—“

            “Goodnight,” the father says, dismissal clear in his tone.

            Kirk pauses. The boy—Sammy? Turns to grab the handle of the door.

            _Sorry_ he mouths, and pulls the door close with a quiet click.

            “What a bunch of weirdos,” Kirk says to himself, slides his pen into his clipboard, glances at the signature on the lease and feels a little uneasy about the stack of bills he has in an envelope in his pocket.

            He heads to the office anyway to lock it in a drawer. As he’s crossing the street from the apartment building, he sees a figure coming out of the new family’s apartment.

            Kirk looks away, hears the sound of their old, flashy car start up, and purses his lips.

\---

            The next morning, word of the new family has circulated. Taylor’s opening up Doose’s when two tall, strange, _suspicious_ teenage figures appear outside his store’s window.

            “You open?” the one in the leather jacket asks. Rudely.

            Taylor raises an eyebrow.

            “Young man, is there something I can do for you? Besides continuing to let you loiter outside my store.”

            The boy’s eyes narrow, “I asked you if you’re open.”

            Taylor shakes his head, “I don’t know where you’re from, but in Stars Hollow, we take our time. Doose’s will open at 9:00, sharp.”

            “It’s 8:56,” the other boy finally speaks up.

            “Well then you will wait four minutes and then you may come and make your purchases. And I _know_ neither of you are 21, so don’t even try it.”

            “You hear that, Dean?” the boy asks, elbowing the guy in the leather jacket.

            “Shut up, Sammy,” Dean replies quickly.

            Taylor closes the door behind him, locks it, watches the two boys from inside the market for three minutes before begrudgingly moving back to let them in.

            “Such service,” Dean says as he enters, heads for the back of the store immediately while Sam lingers behind, grabs a basket.

            Taylor’s worried that they’ll separate, try to divide and conquer with their delinquency, but he’s relieved to find Sam gravitating back towards Dean immediately.

            He doesn’t watch discreetly. He follows them, five steps behind them, as they grab peanut butter and bread and mac and cheese.

            He doesn’t like the look of them, that’s for sure. Something hungry in their eyes, a little too eager in the way they grab the food. He’s half expecting them to run for the door, despite the way he’s hovering, basket and all, but they head to register.

            Taylor follows behind them, unashamed as he rings up their purchases.

            “$42.50,” he says, almost like a challenge, wondering what item they were going to pretend they didn’t want anymore.

            But the boy Sam smiles and pulls three smooth twenty dollar bills from the wallet he takes from his pocket.

            “Here you go,” he says pleasantly and Taylor sees something else in his eye—pride, maybe, and he thinks ever so briefly that he maybe was a little too hard on the boys.

            He bags their groceries, watches them leaves and Dean says “Can’t believe what a fucking goodie two-shoes you are, Sam,” and Taylor shakes his head, and forgets to be generous.

\---

            Miss Patty helps Sam find the school on the first day. Not that the boy probably needed help, he was heading the right direction, but Miss Patty hurried to catch him when he passed her dance studio.

            “Heading to school, dear?” She asked, and Sam turned, nodded at her with a small, shy smile.

            Patty knew Taylor was being irrational—he seemed like a perfectly nice boy. Handsome and polite, someone Patty could see her sixteen-year-old self liking. Even then she liked boys sweet, she liked boys who were kind and cute and Sam flashed dimples and Patty could imagine herself at sixteen again, chasing after this beautiful boy in school.

            “New to town, I hear?” She says, because she is not sixteen anymore, and what interests her now are stories. She learned how to get men decades ago, getting stories out of people was something else entirely.

            “Yeah,” Sam says again, not rude, just shy, Patty figures and she nods encouragingly.

            “It’s a lovely high school. Lovely teachers. Only a few rotten kids. You’ll have to tell me what you think though, an outsiders perspective is always so refreshing.”

            The boy nodded, and from behind them, Patty hears the padding of footsteps.

            “Yo, Sammy,” a voice punctuates, two distinct syllables, and the tense, shy boy next to Patty relaxes, smiles.

            Another boy—Dean, if Patty’s remembering the story correctly—makes space for himself on the sidewalk next to Sam and Patty. He looks at directly at Patty till Sam notices.

            “Oh this is—“ Sam starts,

            “Oh, I’m Miss Patty, dear,” Patty says, not the least bit impressed by the stare down the big brother is trying, “So rude of me to not introduce myself,” she continues, prompt hanging in the air.

            “Can we help you with something?” Dean says instead and Patty finds herself smiling.

            “Just pointing your brother in the right direction,” Patty says, “Will you be attending with him?”

            “Sam and I can navigate just fine,” Dean says, nods to her and hooks an arm through Sam’s slimmer one.

            “Ma’am,” he says, first show of manners that must have been taught by someone, and he leads Sam down the street, head close to Sam’s ear as he talks.

            Patty watches them go, heads back into her studio. When she spreads the story she does so with many, many more details because she feels like they are a pair ripe for interpretation.

\---

            Sam Winchester is in Lane’s third period algebra class. She knows because Mr. May made Sam introduce himself and share one fun fact.

            “How tall are you?” Delaney Shrewson asks from the front row,

            “Um, I’m 6’2?” Sam says it like a question and Mr. May, who’s old and kind of a terrible teacher, says,

            “I said a _fun_ fact, Sam. Everyone can see you’re a tall boy.”

            “I’m not very interesting,” Sam says, and then he sits down and reponds to Mr. May’s disapproving glance with a shrug.

            Nevertheless, people are interested in Sam. Lane included. He’s hot and she thinks he’s probably pretty smart because he answers one of Mr. May’s equations correctly on the first try.

            He’s new, too, so no matter how Sam tried to not interest people, it was inevitable. Lane feels a little bad for him.

            She sees him again at lunch, sitting at a nearly empty table with another new boy. Apparently, his brother, from what Lane heard from eavesdropping on Brittany Kepler.

            Lane has this lunch period pretty much alone, but she sits at the table with some of the cheerleaders and one of her friends from church. They talk amongst themselves about the new kids.

            Sam and his brother are only a few tables away so Lane’s a little embarrassed at how loud they’re being.

            “His brother is in my cousin’s shop class and they got paired up for an assignment and apparently he’s super into her,” Lane’s friend from church says, and Lane watches as Sam, a few tables down, seems to tense up.

            Probably heard. How mortifying. Lane says nothing, she doesn’t want Sam to look at her in class and assume she’s some part of this.

            “Yeah, well his brother’s kind of hot, too. Like, in a dorky way,” one of the cheerleaders says, “He’s in my gym period. I tried to talk to him but he’s really quiet. You know what they say about the quiet ones though—“

            Lane hasn’t moved her focus from the boy’s table, and she watches as Sam’s older brother starts to smirk at Sam, says something that makes Sam’s face turn red.

            Then he leans across the table, and slides one hand over Sam’s, wiggling his eyebrows.

            Sam slides his hand away in a delayed kind of reaction, Lane thinks. Like he knew that he should, but not like it was instinct. Dean’s got his head tipped back, laughing, and Sam’s leaning toward him, face breaking out into a wide, dimpled smile.

            Lane doesn’t know what to do with the moment. She tries to pretend she didn’t see, suddenly feeling like that time she walked into an argument between Rory and Lorelai. She felt like she was intruding.

            She doesn’t say anything as the conversation wraps up, and she quietly heads to her next class.

            When she sees Sam in algebra the next morning, she still hasn’t told anyone about what she saw. She looks at him and wonders why interesting people are always so secretive about it. If Lane was interesting, she’d shout it from the rooftops. She wants so, so badly to be interesting. For someone to take _interest_ in her. But Rory has Dean now. She barely listens to Lane anymore and all Lane has is a dismal double date and an even worse hair-touching incident and some days she feels so small that she curls up and listens to Blondie and thinks that even if she were on stage, people would still look right past her.

            She sees Sam in the hallway later in the day. He’s talking to his big brother and he’s looking at Sam like he’s a point of wonder, a big deal, something to really, really watch.

            Lane looks away. 

\---

            The first time Luke meets Dean Winchester, Lorelai and Rory have just left.

            He is, understandably, a little out of it. So when a _kid_ slams his hand on the counter, Luke jumps a little, turns, and instantly dislikes him.

            He’s got the menu closed, and he’s looking down at his menu like he’s not the only person at the counter.

            He looks up, smiles, “Can I get a beer?”

            Luke laughs. 

            “Yeah, sure. As soon as you can get me an ID, Doogie.”

            The kid nods, pulls a wallet out of his back pocket. He makes a show of flipping through it, then hands Luke an ID apparently from Hawaii.

            Luke shakes his head, hands it back to him, “We don’t sell beer. And I’m not an idiot. You’re that new kid. You go to high school. With all the other underage children in this town.”

            Kid shrugs, “Worth a try.”

            “Not here it isn’t—gonna have to ask you to leave.”

            The kids mouth drops, “Seriously, man? It was a fucking joke. I just came here to get some burgers.”

            “ _Shh_ ,” Luke hisses, looking around to make sure none of the Brownies at the table near the back overheard, “What’s wrong with you?”

            The guy looks around slowly, considering before he fixes his face in false revelation, “I’m still lacking two burgers—one medium rare, extra onions, the other medium with extra ketchup.”

            Luke does not like this kid.

            The bell tinkles above the door and another face enters the diner, tall with too-long hair, he catches sight of the guy at the bar and his face lights up. He heads over and plops down at the stool next to him.

            “You got money to pay for those or are all your bills Hawaiian, too?” Luke says.

            “Hawaii has U.S. currency,” the new kid cuts in.

            “Yeah,” the other guy says, “You might be surprised to learn it’s one of the fifty states.”

            Luke glowers, narrows his eyes, turns to place the order anyway.        

            “What took you, Sam-I-Am?” Luke overhears the ID-faking, disrespectful little punk ask his probably-secretly-untrustworthy companion.

            “Had to ask my teacher about some stuff on the syllabus. She wasn’t really helpful it took forever for her to actually answer my question—ugh. Sorry, here now, what’d you get me?”

            “Burger.”

            “ _Dean,”_

“Thought that was what you wanted,” Dean says happily, wraps an arm around Sam and cranes it oddly to ruffle his hair.

            Sam rolls his eyes, ducks out from under the embrace and somehow comes out of it leaning even closer to Dean.

            “I hate you,” Sam says, and Luke focuses back on his work, calls back to Caesar the burger orders.

            The kid’s disrespectful, but it’s still not any of Luke’s business. He hands them their burgers, takes their money, and doesn’t think about them again once they’ve left the diner.

            When Patty and Babette come in later, they sit at the table closet to the counter and loudly discuss the new faces.

            “Haven’t seen the father,” Patty says, “But Kurt says he brought three of them in Sunday.”

            “Oh, poor boys. Who knows where the father is, let alone the mother,” Babette replies. Both women shake their head.

            Luke brings them two cups of water, and doesn’t say anything.

\---

            “Oh!” Rory exclaims, “Sorry!”

            She’s in the bookstore, trying to find some weird student annotated version of Titus Andronicus that Chilton insists she needs.

            Rory realizes almost instantly that’s she’s bumped into Dean Winchester. She’s heard, at this point, all about Dean Winchester. He’s got the leather jacket and handsome face Babette gushed over, but Rory doesn’t think he looks like a troublemaker like Taylor said.

            Still, he just kind of looks at her, head a little tilted, eyes narrowed.

            Rory reaches behind where Dean's standing and grips the spine of the book she's looking for.

            “Excuse me,” She says, embarrassed “I just need, um—be out of your way.”

            “Wait,” he says as Rory makes her hasty retreat, and Rory whips back around. Something about the whole thing makes her a little nervous.

            “You live here, right?” Dean said gruffly.

            “Yeah!”

            Rory cringes. She sounds like some kind of over-eager puppy, god.

            “Do you…come here a lot?” Dean says, sort of like it pains him.

            Rory blushes, “Yes? Yes. I do—with my boyfriend--me and my boyfriend come here a lot.”

            Dean huffs out a breath, “I’m not trying to—I mean I get that it sounds like that but just—could you like, fucking help me out? The guy up front just looks at me like I’m gonna steal something.”

            “Oh!” Rory says, didn’t realize she could get any redder, could she _be_ any self involved, “Of course! Walt’s not bad he’s just had a long string of petty gum shoplifting from the middle school kids—kind of a dare type thing, you know—God, you don’t care. Sorry.”

            Dean stares at her.

            “What are you looking for?”

            “Sense and Sensibility,” Dean says in a deadpan.

            Rory bursts out laughing. Then she takes in Dean’s serious, slightly uncomfortable, and tries to get herself back under control.

            “I’m sorry! Really! You just—you don’t _look_ like you’d get all worked up over the fate of Elinor,”

            “What?” Dean says.

            “Elinor and Edward? Wait you haven’t read it yet. I’m sorry, of course you don’t know. You’re going to love it, though. Good choice. Jane Austen is a good choice for everyone.”

            “It’s not for me.”

            “Oh.”

            Dean fidgets, actually _fidgets,_ “You like it, though?”

            “Oh yeah! It’s the best.”

            “Okay. Good. You seem like you’d know.”

            “I would.”

            Dean smiles, a tight kind of smile that seems a little unsure. It looks weird on his face, “Can you show me where it is?”

            Rory nods, leads Dean back to the book, and then walks back with him to the checkout so Walt doesn’t give him any trouble.

            Dean pays with a crisp $50 bill, straight out of his wallet, which Walt holds up to the light for a long couple seconds before accepting.

            They’re exiting the store together when Dean pauses, frowns, and turns right back around.

            Rory considers going her separate way for half a second, “Dean? What’re you doing?”

            “This was a dumb idea,” Dean says.

            “What? The book?” Rory says, “It’s a great book. I promise the book is an excellent idea. Don’t put it back in book purgatory.”

            “It’s just—it’s weird, right?”

            “What?”

            “Giving someone a book.”

            _Oh,_ Rory thinks, puts together the nervousness, the discomfort, the uncertainty.

            “Is it for your girlfriend?”

            Dean’s eyes widen. He visibly swallows, gets his expression back under control, “What if it is?” He says, voice all bravado and Rory suddenly feels a lot more comfortable. She thinks of her own Dean, how weird he always got about that gifts her, no matter how sure it was she was going to love it.

            “I think it’s very romantic.” Rory says.

            “Yeah?” Dean says, something Rory would almost call a flush creeping up his neck.

            “Definitely.”

            “Cool,” Dean says, tension leaving his shoulders, smile a little more at ease.

            “Thanks.” He says as he turns from the door to the bookstore.

            “No problem,” Rory says.

            Dean gives her a little wave, turns to walk the opposite direction down the sidewalk.

            “You should read it sometime!” Rory yells down the street, surprising herself at how loud she is. On the other side of the road, she sees Taylor eye her up.

            Dean looks over his shoulder to make eye contact with her, cool-guy head tilt of acknowledgement.

            Rory is pretty pleased with the interaction, always happy to put two more souls on the path to Jane Austen. She’s kind of feeling like a good matchmaker, too. She’s pretty proud of herself all the way around, she wasn’t even _that_ embarrassing.

            She wonders who the lucky lady is.

\---

         The apartments off Hyde street need to be fumigated, so Lorelai’s been working a ten hour day, trying to get all the angry, itchy people into rooms at the Independence. She’s just wrapping up for the day, the last couple booked in a room that they said was overpriced, so Lorelai had to comp them a meal, when the doors to the inn swing open, ushering in two boys.

 _Oh,_ Lorelai thinks instantly, sizing them up, _those weird new kids._

        “Welcome to the Independence Inn!” She says cheerily, pushing down her exhaustion, “You coming to escape the infestation?”

         The one Lorelai recognizes as Dean steps up the counter, Sam at his shoulder.

        “We would’ve stayed, but they forced us out. Should be fucking illegal.”

        “Huh, well, if you’re looking for some cold, hard justice, I’m afraid the court system around here will get around to it in—well, probably right before hell starts getting a little icy.”

         Sam laughs and Lorelai is struck by how young he looks.

         “Sorry,” he says, “We were, um, wondering what the situation here is, rooms-wise.”

        “We have two rooms available right now, but I’m guessing you boys would like the room with the double beds.”

         “Yeah,” Sam says, “What would that cost?”

         “$250,” Lorelai says and Sam’s smile drops off his face, “A week?” Dean questions.

         “A night.” Lorelai replies, feeling a pit in her stomach that feels suspiciously like guilt. But she doesn’t set the room prices. This one isn’t on her.

         “This is fucking ridiculous,” Dean mutters to Sam, “We pay through the month and they kick us out—fucking scam is what it is,” He wraps a hand around Sam’s elbow, pulls him away from the desk, “C’mon, Sam, we’ll figure something out till Dad gets back.”

         They get about three feet from the desk before Lorelai _feels_ herself open her big, dumb mouth and say “Hey!”

         It’s just—they look so pathetic and young and Sam looks kind of like Rory’s big, dumb boyfriend and the picture they make, standing in the lobby of the Independence with no place to go reminds Lorelai painfully of where she was taken in when she had no where to go at sixteen.

         “If you wanna hang out till I close, I think I have somewhere you can stay.”

         “We don’t need charity,” Dean says, and Sam eyes him as he sighs.

        “That’s really kind of you,” he says, “My brother has no manners. Sorry.”

        “No worries,” Lorelai replies, “I prefer compliments and adoration to thanks anyways.”

         “You look nice today,” Dean says.

         “See? Flattery will get you everywhere.” The phone rings and Lorelai gestures broadly to the couch Sam and Dean should wait on as she talks to someone who got the date of their booking wrong.

          Two hours and one cup of coffee later, Lorelai is on her last task of the day. She looks up to see the boys on the couch she left them on. They’re sitting close together, talking quietly, and they regard her with almost blank expressions as she announces she’s taking them to their room.

          “Wow. Don’t get too excited,” She says.

          They walk behind her as she leads them out the back of the inn.

          “I could be leading you to some Jason Voorhees revenge lodge,” She says as they remain silent.

          Dean barks out a laugh “Wouldn’t be the worst place we’ve slept.”

          “Well, then, I think you’ll be feeling extra luxurious tonight, boys,” Lorelai says, feeling kind of proud of herself for helping these boys out. Obviously, her guilt worked in her favor this time.

          “I used to live here with my daughter, Rory. It’s downright homey.” Lorelai unlocks the door to the shed, and swings it open.

         Everything looks pretty much how Lorelai left it, down to the second hand, full sized bed shoved in the left hand corner.

          Lorelai’s eyes light on it and she gesture awkwardly “Sorry about that—I can get you some extra blankets, maybe a cot or something? Make it very Boxcar children in here. I hear that’s what the kids are into now-a-days.”

          Lorelai looks at Sam and quiets because the kid looks downright ecstatic.

           Dean’s looking, too, Lorelai notices, and he’s smiling in a weird, soft way that makes Lorelai feel sort of fuzzy “No, this is great. Thank you. Seriously.”

          “No problem,” Lorelai says quietly. It feels for a minute like they’re under some kind of spell—Lorelai always thought this shed was special, like it felt like home to whoever came in.

          Except her mother, of course, but whatever.

          “Well,” Lorelai says, hesitant to break whatever spell Sam’s under as he looks around the little room, “You guys can stay here as till the apartment situation is sorted out. And, uh, I’ll have our chef, Sookie, send over some food, annnnd” Lorelai clicks her tongue, trying to remember if there’s anything else, and Sam jumps a little. He turns to her, and Lorelai smiles in spite of her best intentions and finishes loudly “Welp, guess that’s it, goodnight!”

          “This is awesome,” Sam says and Lorelai waves a little awkwardly as she heads out the door.

          “You’re such a fucking loser,” Lorelai hears as she makes to slide the door closed behind her. It sticks a little, and she turns to make sure it slides closed all the way, keep the draft out.

          Through the small opening left, Lorelai sees Sam’s smiling kind of goofily, Dean smirking into his face. His arms draped over Sam’s shoulder, and as she slides the door the rest of the way closed, he leans down to peck Sam on the lips.

 _Huh,_ Lorelai thinks, her only vague discomfort at the fact that she’s intruding, _Well, that makes sense._

           

           


End file.
